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Method for preparing 3, 3- diphenyl propanol

A technology of diphenylpropanol and diphenylpropionic acid, which is applied in 3 fields, can solve the problems of non-compliance with green production requirements, difficult reaction control, poor production conditions, etc., and achieve stable and reliable product quality, easy recycling, The effect of fast reaction rate

Inactive Publication Date: 2014-07-30
湖北远成赛创科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this process has many steps and poor production conditions. In the synthesis process, catalysts such as concentrated sulfuric acid and metal sodium are successively used, which makes the reaction difficult to control, the product yield is low, post-processing is troublesome, the cost is high, and the pollution is serious. Green Production Requirements

Method used

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  • Method for preparing 3, 3- diphenyl propanol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] 1) Preparation of 3,3-diphenylpropionic acid (III):

[0026] Mix 31.2 g (0.4 mol) of benzene with 9.7 g of [bmim]Cl / AlCl 3 Mix the ionic liquids, raise the temperature to 70-80°C, add 7.4 grams (0.05 moles) of cinnamic acid in 4 batches within 0.5 hours; after the addition, heat up and reflux for 2 hours; after the reaction is complete, add 50 ml of water, stir well and let stand Layering, the water phase is a mixture of ionic liquid and water, which can be recycled after dehydration by vacuum distillation; the organic phase is recovered by vacuum distillation to recover unreacted benzene, and the obtained solid is a crude product, which is recrystallized with methanol and dried to obtain 3, 9.1 g (0.04 mol) of 3-diphenylpropionic acid, yield 80.4%.

[0027] 2) 3, the preparation of 3-diphenylpropanol (I):

[0028] Add 9.1 grams (0.04 moles) of 3,3-diphenylpropionic acid into 30 milliliters of anhydrous tetrahydrofuran, add 1.7 grams (0.044 moles) of sodium borohydrid...

Embodiment 2

[0030] 1) Preparation of 3,3-diphenylpropionic acid (III):

[0031] Mix 70.3 grams (0.9 moles) of benzene with 25.5 grams of [bmim]Cl / AlCl 3 Mix the ionic liquids, raise the temperature to 70-80°C, add 14.8 grams (0.1 moles) of cinnamic acid in 5 batches within 1.0 hour; after the addition, heat up and reflux for 4 hours; after the reaction is complete, add 100 ml of water, stir well and let stand Layering, the water phase is a mixture of ionic liquid and water, which can be recycled after dehydration by vacuum distillation; the organic phase is recovered by vacuum distillation to recover unreacted benzene, and the obtained solid is a crude product, which is recrystallized with methanol and dried to obtain 3, 18.5 g (0.082 mol) of 3-diphenylpropionic acid, the yield was 81.8%.

[0032] 2) 3, the preparation of 3-diphenylpropanol (I):

[0033] Add 18.5 grams (0.082 moles) of 3,3-diphenylpropionic acid into 60 milliliters of anhydrous ethylene glycol dimethyl ether, add 3.7 gr...

Embodiment 3

[0035] 1) Preparation of 3,3-diphenylpropionic acid (III):

[0036] Mix 156.2 grams (2.0 moles) of benzene with 65.0 grams of [bmim]Cl / AlCl 3 Mix the ionic liquids, heat up to 70-80°C, add 29.6 grams (0.2 moles) of cinnamic acid in 5 batches within 1.0 hour; after the addition, heat up and reflux for 3 hours; after the reaction is complete, add 200 ml of water, stir well and let stand Layering, the water phase is a mixture of ionic liquid and water, which can be recycled after dehydration by vacuum distillation; the organic phase is recovered by vacuum distillation to recover unreacted benzene, and the obtained solid is a crude product, which is recrystallized with methanol and dried to obtain 3, 37.2 g (0.164 mol) of 3-diphenylpropionic acid, yield 82.2%.

[0037] 2) 3, the preparation of 3-diphenylpropanol (I):

[0038]Add 37.2 grams (0.164 moles) of 3,3-diphenylpropionic acid into 120 milliliters of anhydrous ethylene glycol dimethyl ether, add 8.1 grams (0.213 moles) of ...

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Abstract

The invention provides a method for preparing 3, 3- diphenyl propanol, which comprises the following steps of: 1) taking cinnamic acid and benzene as raw materials; carrying out reflux reaction for 2-4hours under the action of ionic liquid chloro 1-methyl-3-buthylimidazole-aluminium trichloride, and thereby preparing 3, 3-diphenyl propionic acid; 2) dissolving the prepared 3, 3-diphenyl propionic acid into ether solvent, and reacting for 2-4hours under the action of sodium / iodine borohydride; and preparing the 3, 3-diphenyl propanol by purification. The method is low in cost of raw materials and mild in reaction condition; the 3, 3-diphenyl propanol is prepared by two-step reaction; the method is simple, easy to operate, high in yield and stable and reliable in product quality; and environmental pollution is not caused by the method, so that the method is a green synthesis method.

Description

technical field [0001] The invention relates to a method for preparing an organic synthesis intermediate, in particular to a method for preparing 3,3-diphenylpropanol. Background technique [0002] 3,3-diphenylpropanol, also known as 1-hydroxy-3,3-diphenylpropane, is an intermediate in organic synthesis and is mainly used in the fields of medicine and chemical industry. For example, in medicine, 3,3-diphenylpropanol is used in the preparation of cardiovascular drug prenylamine lactate, which has the advantages of low cost, high yield, and small side effects. [0003] At present, the method of 3,3-diphenylpropanol mainly adopts the alkylation reaction of cinnamic acid with benzene under the participation of anhydrous aluminum trichloride to generate 3,3-diphenylpropionic acid, and then converts 3,3-diphenylpropanol A three-step synthesis method of esterification of phenylpropionic acid and ethanol under the action of concentrated sulfuric acid, and then reduction with ethano...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C33/24C07C29/147
Inventor 叶思朱如慧杨洁韩洪杰徐海林
Owner 湖北远成赛创科技有限公司
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